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Positively charged water-soluble prodrugs of diclofenac with very fast skin penetration rate

A technology for transdermal administration of diclofenac, which is applied in the direction of skin diseases, diseases, antipyretics, etc., and can solve problems such as difficult administration of diclofenac

Pending Publication Date: 2009-08-05
TECHFIELDS BIOCHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, it is difficult to administer therapeutically effective plasma concentrations of diclofenac in the host by formulation methods

Method used

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  • Positively charged water-soluble prodrugs of diclofenac with very fast skin penetration rate
  • Positively charged water-soluble prodrugs of diclofenac with very fast skin penetration rate
  • Positively charged water-soluble prodrugs of diclofenac with very fast skin penetration rate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment approach

[0061] Preparation of dimethylaminoethyl 2-[(2,6-dichlorophenyl)amino]phenylacetate acetate

[0062] 35.1 g (0.1 mol) of 2-[(2,6-dichlorophenyl)amino]phenylacetyl chloride hydrochloride was dissolved in 100 ml of acetone. The mixture was cooled to 0°C. 8.9 g (0.1 mol) of N,N-dimethylaminoethanol was added to the reaction mixture. Add 20g of sodium bicarbonate and 100ml of water to the mixture. The mixture was stirred at room temperature for 3 hours. The solvent was evaporated to dryness. 100ml of acetone was added to the reaction mixture. The solid by-product was removed by filtration and washed 3 times with 30 ml of acetone. 6g of acetic acid was stirred into the mixture. The organic solvent was evaporated to dryness. After drying, 38 g of the hygroscopic target product was obtained with a yield of 88.9%. Solubility in water: 410mg / ml; Elemental analysis: C 20 h 24 Cl 2 N 2 o 4 ;Molecular weight: 427.32. Theoretical value (%) C: 56.21; H: 5.66; Cl: 16.59, N: 6.5...

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Abstract

The novel positively charged pro-drugs of diclofenac in the general formula(1) 'Structure 1' were designed and synthesized. The compounds of the general formula(1) 'Structure 1' indicated above can be prepared from functional derivatives of diclofenac (for example acid halides or mixed anhydrides), by reaction with suitable alcohols, thiols, or amines. The positively charged amino groups of these pro-drugs not only largely increases the solubility of the drugs in water, but also bonds to the negative charge on the phosphate head group of membranes and push the pro-drug into the cytosol. The experiment results suggest that the pro-drug, diethylaminoethyl 2[(2,6-dichlorophenyl)amino]benzene acetate.AcOH diffuses through human skin ~250 times faster than do 2[(2,6-dichlorophenyl)amino]benzene acetic acid (diclofenac) and ethyl 2[(2,6-dichlorophenyl)amino]benzene acetate. In plasma, more than 90% of these pro-drugs can change back to the drug in a few minutes. The prodrugs can be used medicinally in treating any diclofenac-treatable conditions in humans or animals and be administered not only orally, but also transdermally for any kind of medical treatments and avoid most of the side effects of diclofenac, most notably GI disturbances such as dyspepsia, gastroduodenal bleeding, gastric ulcerations, and gastritis. Controlled transdermal administration systems of the prodrug enables the diclofenac to reach constantly optimal therapeutic blood levels to increase effectiveness and reduce the side effects of diclofenac.

Description

technical field [0001] The present invention relates to positively charged water-soluble prodrugs of 2-[(2,6-dichlorophenyl)amino]phenylacetic acid (diclofenac) and any diclofenac-therapeutic prodrugs thereof for medical use in the treatment of humans or animals. State medical use. Specifically, the present invention aims to overcome the side effects caused by the use of diclofenac. These prodrugs can be administered orally or transdermally. technical background [0002] Diclofenac is a nonsteroidal anti-inflammatory drug of the aryl and heterocyclic aryl acetate class. Diclofenac was synthesized for the first time in 1969 (A. Sallman and R. Pfister, Ger. Patent No. 1,815,802). Diclofenac is available in 120 different countries and is probably the most commonly used NSAID in the world. Diclofenac has the aryl alkanoic acid and anthranilic acid structures of anti-inflammatory drugs, and has anti-inflammatory, analgesic and antipyretic effects. In terms of analgesia, the ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C215/40C07C215/42
CPCC07C229/42C07C237/20A61P1/04A61P11/06A61P15/08A61P17/02A61P17/10A61P19/02A61P25/06A61P27/02A61P29/00A61P35/00A61P43/00
Inventor 于崇曦徐丽娜
Owner TECHFIELDS BIOCHEM CO LTD
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